Water → HCID 58501747, compound

HRID 625655Notes

Reaction equation

HRID 625655 reaction equation
O.[Li+:2].[OH-].[N:4]1([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:8]([C:9]([O:11]C)=[O:10])[CH2:7][CH:6]=[N:5]1.Cl.O>CO>[C:16]([O:15][C:13]([N:4]1[C@H:8]([C:9]([O-:11])=[O:10])[CH2:7][CH2:6][NH:5]1)=[O:14])([CH3:19])([CH3:17])[CH3:18].[Li+:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 21885828Hydrate;hydrochlorideHCID 58501784HCID 58501784, compound

Product 1

HCID 58501747HCID 58501747, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A water (5 mL) solution of LiOH (0.146 g, 6.09 mmol) was added to a methanol (5 mL) solution of (S)-1-tert-butyl 5-methyl 1H-pyrazole-1,5(4H,5H)-dicarboxylate (0.76 g, 3.11 mmol), and stirred at ambient conditions for ˜7 h. The reaction mixture was cooled with an ice-water bath, and HCl/H2O (3 mL of 1.00 N; 3.0 mmol) was added dropwise and stirred for a few minutes. Then, the volatile component was removed in vacuo and the resultant viscous oil was exposed to high vacuum to afford lithium (S)-2-(tert-butoxycarbonyl)pyrazolidine-3-carboxylate as a white foam, which was used without further purification. 1H NMR (DMSO-d6, δ=2.50 ppm, 400 MHz) for crude sample: 3.98 (dd, J=8.5, 6.3, 1H), 2.86-2.74 (m, 2H), 2.45 (s, 3H), 2.25-2.17 (m, 1H), 2.10-2.02 (m, 1H), 1.35 (s, 9H). LC-MS: Anal. Calcd. for [M+H]+ C10H19N2O4: 231.13. found 231.21.

Workup

  1. temperatureThe reaction mixture was cooled with an ice-water bath
  2. stirringstirred for a few minutes
  3. customThen, the volatile component was removed in vacuo

Sources & evidence

ORD record
ord-c0f115914e614f3c85a787e3d655bdaf
Source dataset
uspto-grants-2016_04
Patent number
US09303007B2

Reaction notes

Loading…